Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Patent
1997-05-20
1998-09-29
Davis, Zinna Northington
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
514242, 514247, 514255, 514256, 514261, 514307, 514311, 514357, 514411, 544182, 544215, 544238, 544277, 544335, 544358, 546145, 546175, 546336, 548505, C07D23932, C07D21384, A01N 4348, A01N 4364
Patent
active
058146334
DESCRIPTION:
BRIEF SUMMARY
This is a National Stage Application under 35 U.S.C. .sctn.371, based on International Application No. PCT/EP 95/04,430, filed Nov. 10, 1995.
The present invention relates to iminooxymethyleneanilides of the formula I ##STR2## where the index and the substituents have the following meanings: n is 0, 1, 2, 3 or 4, it being possible for the substituents R to be different if n is greater than 1; or to two adjacent ring atoms, which contains three or four members from the group consisting of 3 or 4 carbon atoms, and 2 or 3 carbon atoms and 1 or 2 nitrogen, oxygen and/or sulfur atoms, it being possible for this bridge, together with the ring to which it is bonded, to form a partially unsaturated or aromatic radical; alkylcarbonyl or alkoxycarbonyl; case where X is NR.sup.a, additionally hydrogen; alkylthio, haloalkylthio or cycloalkyl; system which is substituted by customary groups,
WO-A 93/15,046 discloses anilides having fungicidal activity.
It is an object of the present invention to make available active compounds having improved activity.
We have found that this object is achieved by the compounds I defined at the beginning. We have additionally found processes for their preparation, compositions containing them and methods for their use, in particular for controlling animal pests and harmful fungi.
The compounds I are obtainable by various methods. Compounds I, where R.sup.1 is not hydrogen, are particularly advantageously obtained by reacting a methyleneanilide of the formula II with an oxime of the formula III or its salt. ##STR3##
L.sup.1 in the formula II is a leaving group, ie. a nucleophilically replaceable group such as halogen (eg. chlorine, bromine or iodine), or an alkyl- or arylsulfonate (eg. methylsulfonate, trifluoromethylsulfonate, phenylsulfonate or 4-methylphenylsulfonate).
The oximes III can also be used in the form of their salts, eg. with inorganic acids, such as hydrochlorides, hydrobromides, hydrosulfates and hydrophosphonates.
The reaction of the compounds II and III is customarily carried out at from 0.degree. C. to 80.degree. C., preferably 20.degree. C. to 60.degree. C., in an inert solvent in the presence of a base.
Suitable solvents are aromatic hydrocarbons such as toluene, o-, m- and p-xylene, halogenated hydrocarbons such as methylene chloride, chloroform and chlorobenzene, ethers such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran, nitrites such as acetonitrile and propionitrile, alcohols such as methanol, ethanol, n-propanol, i-propanol, n-butanol and tert-butanol, ketones such as acetone and methyl ethyl ketone, and dimethyl sulfoxide, dimethylformamide, dimethylacetamide, 1,3-dimethylimidazolidin-2-one and 1,2-dimethyltetrahydro-2(1H)-pyrimidine, preferably methylene chloride, acetone, toluene, tert-butyl methyl ether and dimethylformamide. Mixtures of the solvents mentioned can also be used.
Suitable bases are generally inorganic compounds such as alkali metal and alkaline earth metal hydroxides (eg. lithium hydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide), alkali metal and alkaline earth metal oxides (eg. lithium oxide, sodium oxide, calcium oxide and magnesium oxide), alkali metal and alkaline earth metal hydrides (eg. lithium hydride, sodium hydride, potassium hydride and calcium hydride), alkali metal amides (eg. lithium amide, sodium amide and potassium amide), alkali metal and alkaline earth metal carbonates (eg. lithium carbonate and calcium carbonate) and also alkali metal hydrogen carbonates (eg. sodium hydrogen carbonate), organometallic compounds, in particular alkali metal alkyls (eg. methyllithium, butyllithium and phenyllithium), alkylmagnesium halides (eg. methylmagnesium chloride) and also alkali metal and alkaline earth metal alkoxides (eg. sodium methoxide, sodium ethoxide, potassium ethoxide, potassium tert-butoxide and dimethoxymagnesium), additionally organic bases, eg. tertiary amines such as trimethylamine, triethylamine, triisopropylethylamine and N-methylpiperidine, pyrid
REFERENCES:
patent: 5342837 (1994-08-01), Clough et al.
Derwent Abst. J 5 3116-378.
Synthesis of a series of 5-nitro . . . , Hrelia et al., Mutagenesis vol. 8, No. 3, pp. 183-188, 1993.
Ammermann Eberhard
Gotz Norbert
Lorenz Gisela
Muller Bernd
Rohl Franz
BASF - Aktiengesellschaft
Davis Zinna Northington
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